Abstract
The molecular and electronic structure of the ground state of peroxyacetyl nitrate (PAN) was calculated by the unrestricted Hartree-Fock-Roothaan method with the use of the standard 3–21G and 6–31G basis set. The potential curve of the internal rotation about the peroxide bond of PAN was calculated with the 6–31G basis set. The curve contains two maxima. The ground state of PAN is characterized by a structure in which groups of atoms adjacent to the peroxide bond lie in planes that are perpendicular to each other (the dihedral angle ϱ(COON) is 89.9°). The calculated barriers to rotation are 19.6 and 66.8 kJ mol−1.
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References
V. L. Antonovsky,Khimiya peroksinitratov-komponentov fotokhimicheskogo smoga [Chemistry of Peroxy Nitrates, the Components of Photochemical Smog], Nauka, Moscow, 1989, 109 pp. (in Russian).
E. R. Stephens, E. C. Darley, E. C. Taylor, and W. E. Scott,Int. J. Air Water Pollut., 1951,4, 79.
E. R. Stephens, W. E. Scott, P. L. Hanst, and R. E. Doerr,J. Air Pollut. Control. Assoc., 1956,6, 159.
O. C. Taylor,J. Air Pollut. Control. Assoc., 1969,19, 347.
D. J. Jacob, and S. C. Wafsy,J. Geophys. Res., 1988,93, 1477.
D. Grosjean, E. L. Williams, and E. Grosjean,Environ. Sci. Technol., 1993,27, 830.
K. A. Kourtidis, P. F. Fabian, C. Zerffos, and B. Rappengluck,Tellus, 1993,45B, 442.
H. B. Singh, L. J. Salas, and W. Viezee,Nature, 1986,321, 588.
B. E. Hartsell, V. P. Aneja, and W. A. Lonneman,J. Geophys. Res., 1994,99D, 21.033.
C. W. Spicer, M. W. Holden, and G. W. Keigely,Atmos. Environ., 1983,17, 1055.
H. B. Singh, D. O'Hara, D. Herlth, J. D. Bradshaw, S. T. Sandholm, D. L. Gregory, G. W. Sachse, D. R. Blake, P. S. Critzen, and M. A. Kanakidon,J. Geophys. Res., 1992,97, 16511.
P. E. Perros,J. Geophys. Res., 1994,99D, 8269.
W. J. Moxim, H. Levy, and P. S. Kasibhatla,J. Geophys. Res., 1996,101D, 12.621.
J. J. Orlando, G. S. Tyndalt, and J. B. Calvert,Atmos. Environ., 1992,26A, 3089.
D. Grosjean, E. Grosjean, and E. L. Williams,J. Air Waste Manage Assoc., 1994,44, 391.
F. Zabel,Z. Physik. Chemie, 1995,188, 119.
V. L. Antonovsky,Kinet. Katal., 1995,36, 370[Kinet. Catal. 1995,36, 335 (Engl. Transl.)].
A. G. Kligerman, K. Mottus, and G. L. Erexson,Mutation Res., 1995,341, 199.
V.L. Antonovsky, and K. V. Bozhenko,Tez. dokl. konf. po kvantovoi khimii, stroeniyu i reaktsionnoi sposobnosti molekul [Abstract of Papers, Conf. on Quantum Chemistry, Structure, and Reactivity of Molecules], Izd-vo Rostovskogo Gosuniversiteta, Rostov-on-Don, 1994 4 (in Russian).
K. V. Bozhenko and V. L. Antonovsky,Abstracts of Papers, Am. Conf. on Theoretical Chemistry ACTC, Utah, 1996, P. 1, 20.
V. L. Antonovsky and K. V. Bozhenko,Dokl. Akad. Nauk, 1995,343, 337[Dokl. Phys. Chem., 1995,343, 173 (Engl. Transl.)].
V. L. Antonovsky and K. V. Bozhenko,Izv. Akad. Nauk, Ser. Khim., 1997, 684 [Russ. Chem. Bull.,1997,46, 653 (Engl. Transl.)].
R. P. Saxon and B. Lin,J. Phys. Chem.,1985,89, 1227.
D. G. Hendry and R. A. Kenley,J. Am. Chem. Soc., 1977,99, 3198.
T. Nielsen,Atmos. Environ., 1982,16, 2447
T. M. Kravatz, S. W. Martin, and G. D. Mendenhall,Environ. Sci. Technol., 1980,14, 1262.
J. A. Cudley, W. Bossert, A. Bauder, and H. H. Gu nthard,Chem. Physics, 1976,16, 229.
A. P. Cox and S. Warning,Trans. Faraday Soc., 1971,67, 3441.
Landolt-Börnstein,Numerical Data and Functional Relations in Science and Technology, New Series II/7, 1976, 246.
V. L. Antonovsky,Progress v khimii organicheskikh peroksidov [Progress in the Chemistry of Organic Peroxides], IsNIITENeftekhim, Moscow, 1992, 80 pp. (in Russian).
V. L. Antonovsky, inOrganicheskie i elementoorganicheskie peroksidy. Vestnik Nizhegorodskogo gosuniversiteta [Organic and Organometallic Peroxides, Proceedings of the Nizhnii Novgorod State University], Izd-vo NNGU, Nizhnii Novgorod, 1996, 3 (in Russian).
A. A. Espenbetov, V. A. Filippov, M. Yu. Antipin, V. G. Tsirel'son, Yu. T. Struchkov, and B. S. Svetlov,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 1558 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34, 1425 (Engl. Transl.)].
N. J. Karch, E. T. Koh, B. L. Whitsel, and J. M. McBride,J. Am. Chem. Soc., 1975,97, 6729.
R. M. Minyaev,Usp. Khim., 1994,64, 939 [Russ. Chem. Rev., 1994,64 (Engl. Transl.)].
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 600–604, April, 1998.
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Antonovsky, V.L., Bozhenko, K.V. Ab initio study of the ground state and conformational stability of peroxyacetyl nitrate in internal rotation about the peroxide bond. Russ Chem Bull 47, 578–583 (1998). https://doi.org/10.1007/BF02495956
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DOI: https://doi.org/10.1007/BF02495956